Literature DB >> 17048870

Asymmetric syntheses of (-)-mitorubrin and related azaphilone natural products.

Jianglong Zhu1, John A Porco.   

Abstract

Asymmetric syntheses of (-)-mitorubrin and related azaphilone natural products are reported. Key steps involve copper-mediated, enantioselective oxidative dearomatization to prepare the azaphilone core and olefin cross-metathesis for side-chain installation. [reaction: see text]

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Year:  2006        PMID： 17048870     DOI： 10.1021/ol062233m

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Stereodivergent, Chemoenzymatic Synthesis of Azaphilone Natural Products.

Authors:  Joshua B Pyser; Summer A Baker Dockrey; Attabey Rodríguez Benítez; Leo A Joyce; Ren A Wiscons; Janet L Smith; Alison R H Narayan
Journal:  J Am Chem Soc       Date:  2019-11-06       Impact factor: 15.419

3.  Reengineering an azaphilone biosynthesis pathway in Aspergillus nidulans to create lipoxygenase inhibitors.

Authors:  Amber D Somoza; Kuan-Han Lee; Yi-Ming Chiang; Berl R Oakley; Clay C C Wang
Journal:  Org Lett       Date:  2012-02-01       Impact factor: 6.005

Review 4.  Chemoenzymatic Total Synthesis of Natural Products.

Authors:  Suman Chakrabarty; Evan O Romero; Joshua B Pyser; Jessica A Yazarians; Alison R H Narayan
Journal:  Acc Chem Res       Date:  2021-02-18       Impact factor: 22.384

5.  Synthesis of azaphilone-based chemical libraries.

Authors:  Mathieu Achard; Aaron B Beeler; John A Porco
Journal:  ACS Comb Sci       Date:  2012-02-24       Impact factor: 3.784

Review 6.  Dearomatization strategies in the synthesis of complex natural products.

Authors:  Stéphane P Roche; John A Porco
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-19       Impact factor: 15.336

7.  Synthesis of the azaphilones (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization.

Authors:  Andrew R Germain; Daniel M Bruggemeyer; Jianglong Zhu; Cedric Genet; Peter O'Brien; John A Porco
Journal:  J Org Chem       Date:  2011-03-14       Impact factor: 4.354

8.  Enantioselective Synthesis of Hydrobenzofuranones Using an Asymmetric Desymmetrizing Intramolecular Stetter Reaction of Cyclohexadienones.

Authors:  Qin Liu; Tomislav Rovis
Journal:  Org Process Res Dev       Date:  2007       Impact factor: 3.317

9.  Asperlones A and B, dinaphthalenone derivatives from a mangrove endophytic fungus Aspergillus sp. 16-5C.

Authors:  Ze'en Xiao; Shao'e Lin; Chunbing Tan; Yongjun Lu; Lei He; Xishan Huang; Zhigang She
Journal:  Mar Drugs       Date:  2015-01-13       Impact factor: 5.118

Review 10.  Polyketides, toxins and pigments in Penicillium marneffei.

Authors:  Emily W T Tam; Chi-Ching Tsang; Susanna K P Lau; Patrick C Y Woo
Journal:  Toxins (Basel)       Date:  2015-10-30       Impact factor: 4.546
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